ES2373865T3 - Uso de derivados canfolénicos como componentes de fragancia en perfumeria y aromatización. - Google Patents

Uso de derivados canfolénicos como componentes de fragancia en perfumeria y aromatización. Download PDF

Info

Publication number: ES2373865T3
Authority: ES; Spain
Prior art keywords: trimethyl; hex; enyl; cyclopent; enal
Prior art date: 2006-12-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES07847910T

Other languages

English (en)

Spanish (es)

Inventor

Jean Mane

Caroline Plessis

Jean-Jacques Chanot

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

V Mane Fils SAS

Original Assignee

V Mane Fils SAS

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-12-08

Filing date

2007-12-06

Publication date

2012-02-09

2007-12-06 Application filed by V Mane Fils SAS filed Critical V Mane Fils SAS

2007-12-06 Priority claimed from PCT/EP2007/063435 external-priority patent/WO2008068310A1/en

2012-02-09 Application granted granted Critical

2012-02-09 Publication of ES2373865T3 publication Critical patent/ES2373865T3/es

Status Active legal-status Critical Current

2027-12-06 Anticipated expiration legal-status Critical

Links

239000003205 fragrance Substances 0.000 title claims description 20
238000005899 aromatization reaction Methods 0.000 title description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 23
CFXOOALSKOYANW-UHFFFAOYSA-N 3-methyl-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enal Chemical compound O=CCC(C)C=CCC1CC=C(C)C1(C)C CFXOOALSKOYANW-UHFFFAOYSA-N 0.000 claims abstract description 17
229920006395 saturated elastomer Polymers 0.000 claims abstract description 14
125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
239000000796 flavoring agent Substances 0.000 claims abstract description 4
235000013355 food flavoring agent Nutrition 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
238000002360 preparation method Methods 0.000 claims description 22
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 20
-1 cyclopent-3-enyl Chemical group 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
241000218236 Cannabis Species 0.000 claims description 13
235000019568 aromas Nutrition 0.000 claims description 6
239000006071 cream Substances 0.000 claims description 6
235000019645 odor Nutrition 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
ASSLVOHPKGZROT-UHFFFAOYSA-N 6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enal Chemical compound CC1=CCC(CC=CCCC=O)C1(C)C ASSLVOHPKGZROT-UHFFFAOYSA-N 0.000 claims description 5
AUFHDPCEVJQOJO-UHFFFAOYSA-N 6-(2,2,3-trimethylcyclopentyl)hex-4-enenitrile Chemical compound CC1CCC(CC=CCCC#N)C1(C)C AUFHDPCEVJQOJO-UHFFFAOYSA-N 0.000 claims description 5
239000002537 cosmetic Substances 0.000 claims description 5
229910052943 magnesium sulfate Inorganic materials 0.000 claims description 5
235000019341 magnesium sulphate Nutrition 0.000 claims description 5
235000015067 sauces Nutrition 0.000 claims description 5
ASSLVOHPKGZROT-AGLBCWCQSA-N (z)-6-[(1s)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enal Chemical compound CC1=CC[C@H](C\C=C/CCC=O)C1(C)C ASSLVOHPKGZROT-AGLBCWCQSA-N 0.000 claims description 4
DTHJNQYLRVNOCX-UHFFFAOYSA-N 6-(2,2,3-trimethylcyclopentyl)hex-4-enal Chemical compound CC1CCC(CC=CCCC=O)C1(C)C DTHJNQYLRVNOCX-UHFFFAOYSA-N 0.000 claims description 4
238000004140 cleaning Methods 0.000 claims description 4
230000001815 facial effect Effects 0.000 claims description 4
239000006210 lotion Substances 0.000 claims description 4
239000003921 oil Substances 0.000 claims description 4
239000002304 perfume Substances 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
ASSLVOHPKGZROT-RYWCDNDXSA-N (z)-6-[(1r)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enal Chemical compound CC1=CC[C@@H](C\C=C/CCC=O)C1(C)C ASSLVOHPKGZROT-RYWCDNDXSA-N 0.000 claims description 3
KIBZVFGCHVKPHT-UHFFFAOYSA-N 2,4-dimethyl-6-(2,2,3-trimethylcyclopentyl)hexanal Chemical compound O=CC(C)CC(C)CCC1CCC(C)C1(C)C KIBZVFGCHVKPHT-UHFFFAOYSA-N 0.000 claims description 3
AKSNWXLGEPAJHJ-UHFFFAOYSA-N 4-ethyl-6-(2,2,3-trimethylcyclopentyl)hexanenitrile Chemical compound N#CCCC(CC)CCC1CCC(C)C1(C)C AKSNWXLGEPAJHJ-UHFFFAOYSA-N 0.000 claims description 3
AZDPQCUMJKQEQL-UHFFFAOYSA-N 4-methyl-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enenitrile Chemical compound N#CCCC(C)=CCC1CC=C(C)C1(C)C AZDPQCUMJKQEQL-UHFFFAOYSA-N 0.000 claims description 3
JTUFNEXXQAOHLZ-UHFFFAOYSA-N 4-methyl-6-(2,2,3-trimethylcyclopentyl)hex-3-enenitrile Chemical compound CC1CCC(CCC(C)=CCC#N)C1(C)C JTUFNEXXQAOHLZ-UHFFFAOYSA-N 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
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230000000873 masking effect Effects 0.000 claims description 3
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SKSCBPUOSNVLNV-KPKJPENVSA-N (e)-4-methyl-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enal Chemical compound O=CCCC(/C)=C/CC1CC=C(C)C1(C)C SKSCBPUOSNVLNV-KPKJPENVSA-N 0.000 claims description 2
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AUFHDPCEVJQOJO-GQCTYLIASA-N (e)-6-(2,2,3-trimethylcyclopentyl)hex-4-enenitrile Chemical compound CC1CCC(C\C=C\CCC#N)C1(C)C AUFHDPCEVJQOJO-GQCTYLIASA-N 0.000 claims description 2
HEJSAKROAFFXKZ-DIECRNLCSA-N (e)-6-[(1r)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enenitrile Chemical compound CC1=CC[C@@H](C\C=C\CCC#N)C1(C)C HEJSAKROAFFXKZ-DIECRNLCSA-N 0.000 claims description 2
HEJSAKROAFFXKZ-BPJJOFIESA-N (e)-6-[(1s)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enenitrile Chemical compound CC1=CC[C@H](C\C=C\CCC#N)C1(C)C HEJSAKROAFFXKZ-BPJJOFIESA-N 0.000 claims description 2
SKSCBPUOSNVLNV-GHXNOFRVSA-N (z)-4-methyl-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enal Chemical compound O=CCCC(/C)=C\CC1CC=C(C)C1(C)C SKSCBPUOSNVLNV-GHXNOFRVSA-N 0.000 claims description 2
AZDPQCUMJKQEQL-GHXNOFRVSA-N (z)-4-methyl-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enenitrile Chemical compound N#CCCC(/C)=C\CC1CC=C(C)C1(C)C AZDPQCUMJKQEQL-GHXNOFRVSA-N 0.000 claims description 2
ASSLVOHPKGZROT-XQRVVYSFSA-N (z)-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enal Chemical compound CC1=CCC(C\C=C/CCC=O)C1(C)C ASSLVOHPKGZROT-XQRVVYSFSA-N 0.000 claims description 2
AUFHDPCEVJQOJO-XQRVVYSFSA-N (z)-6-(2,2,3-trimethylcyclopentyl)hex-4-enenitrile Chemical compound CC1CCC(C\C=C/CCC#N)C1(C)C AUFHDPCEVJQOJO-XQRVVYSFSA-N 0.000 claims description 2
HEJSAKROAFFXKZ-RYWCDNDXSA-N (z)-6-[(1r)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enenitrile Chemical compound CC1=CC[C@@H](C\C=C/CCC#N)C1(C)C HEJSAKROAFFXKZ-RYWCDNDXSA-N 0.000 claims description 2
HEJSAKROAFFXKZ-AGLBCWCQSA-N (z)-6-[(1s)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enenitrile Chemical compound CC1=CC[C@H](C\C=C/CCC#N)C1(C)C HEJSAKROAFFXKZ-AGLBCWCQSA-N 0.000 claims description 2
JUFXQKKMGHPBCN-UHFFFAOYSA-N 3-methyl-6-(2,2,3-trimethylcyclopentyl)hexanal Chemical compound O=CCC(C)CCCC1CCC(C)C1(C)C JUFXQKKMGHPBCN-UHFFFAOYSA-N 0.000 claims description 2
SXXDYTDAQLGNHE-UHFFFAOYSA-N 4-(6,6-diethoxyhex-2-enyl)-1,5,5-trimethylcyclopentene Chemical compound CCOC(OCC)CCC=CCC1CC=C(C)C1(C)C SXXDYTDAQLGNHE-UHFFFAOYSA-N 0.000 claims description 2
SXXDYTDAQLGNHE-CMDGGOBGSA-N 4-[(e)-6,6-diethoxyhex-2-enyl]-1,5,5-trimethylcyclopentene Chemical compound CCOC(OCC)CC\C=C\CC1CC=C(C)C1(C)C SXXDYTDAQLGNHE-CMDGGOBGSA-N 0.000 claims description 2
SXXDYTDAQLGNHE-HJWRWDBZSA-N 4-[(z)-6,6-diethoxyhex-2-enyl]-1,5,5-trimethylcyclopentene Chemical compound CCOC(OCC)CC\C=C/CC1CC=C(C)C1(C)C SXXDYTDAQLGNHE-HJWRWDBZSA-N 0.000 claims description 2
FGLZUGWBMWQQRU-UHFFFAOYSA-N 4-ethyl-6-(2,2,3-trimethylcyclopentyl)hexanal Chemical compound O=CCCC(CC)CCC1CCC(C)C1(C)C FGLZUGWBMWQQRU-UHFFFAOYSA-N 0.000 claims description 2
SKSCBPUOSNVLNV-UHFFFAOYSA-N 4-methyl-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enal Chemical compound O=CCCC(C)=CCC1CC=C(C)C1(C)C SKSCBPUOSNVLNV-UHFFFAOYSA-N 0.000 claims description 2
SATSLDXTNFESAE-UHFFFAOYSA-N 4-methyl-6-(2,2,3-trimethylcyclopentyl)hexanal Chemical compound O=CCCC(C)CCC1CCC(C)C1(C)C SATSLDXTNFESAE-UHFFFAOYSA-N 0.000 claims description 2
ASSLVOHPKGZROT-CYBMUJFWSA-N 6-[(1r)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enal Chemical compound CC1=CC[C@@H](CC=CCCC=O)C1(C)C ASSLVOHPKGZROT-CYBMUJFWSA-N 0.000 claims description 2
HEJSAKROAFFXKZ-CYBMUJFWSA-N 6-[(1r)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enenitrile Chemical compound CC1=CC[C@@H](CC=CCCC#N)C1(C)C HEJSAKROAFFXKZ-CYBMUJFWSA-N 0.000 claims description 2
ASSLVOHPKGZROT-ZDUSSCGKSA-N 6-[(1s)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enal Chemical compound CC1=CC[C@H](CC=CCCC=O)C1(C)C ASSLVOHPKGZROT-ZDUSSCGKSA-N 0.000 claims description 2
HEJSAKROAFFXKZ-ZDUSSCGKSA-N 6-[(1s)-2,2,3-trimethylcyclopent-3-en-1-yl]hex-4-enenitrile Chemical compound CC1=CC[C@H](CC=CCCC#N)C1(C)C HEJSAKROAFFXKZ-ZDUSSCGKSA-N 0.000 claims description 2
MDUITGNQUCLKIJ-UHFFFAOYSA-N 7-(2,2,3-trimethylcyclopent-3-en-1-yl)hept-5-en-2-one Chemical compound CC(=O)CCC=CCC1CC=C(C)C1(C)C MDUITGNQUCLKIJ-UHFFFAOYSA-N 0.000 claims description 2
235000002637 Nicotiana tabacum Nutrition 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
230000001166 anti-perspirative effect Effects 0.000 claims description 2
239000003213 antiperspirant Substances 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
239000000306 component Substances 0.000 claims description 2
239000012141 concentrate Substances 0.000 claims description 2
239000003599 detergent Substances 0.000 claims description 2
FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 2
238000007598 dipping method Methods 0.000 claims description 2
235000013305 food Nutrition 0.000 claims description 2
239000000499 gel Substances 0.000 claims description 2
235000013336 milk Nutrition 0.000 claims description 2
210000004080 milk Anatomy 0.000 claims description 2
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HEJSAKROAFFXKZ-XQRVVYSFSA-N (z)-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enenitrile Chemical compound CC1=CCC(C\C=C/CCC#N)C1(C)C HEJSAKROAFFXKZ-XQRVVYSFSA-N 0.000 claims 1
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241000208125 Nicotiana Species 0.000 claims 1
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125000006726 (C1-C5) alkenyl group Chemical group 0.000 abstract 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 82
150000001875 compounds Chemical class 0.000 description 49
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 21
238000005160 1H NMR spectroscopy Methods 0.000 description 21
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 12
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238000000034 method Methods 0.000 description 9
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241001465754 Metazoa Species 0.000 description 4
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JLASANFKJMCZHO-UHFFFAOYSA-M 3-cyanopropyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC#N)C1=CC=CC=C1 JLASANFKJMCZHO-UHFFFAOYSA-M 0.000 description 3
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ASSLVOHPKGZROT-GQCTYLIASA-N (e)-6-(2,2,3-trimethylcyclopent-3-en-1-yl)hex-4-enal Chemical compound CC1=CCC(C\C=C\CCC=O)C1(C)C ASSLVOHPKGZROT-GQCTYLIASA-N 0.000 description 1
DTHJNQYLRVNOCX-GQCTYLIASA-N (e)-6-(2,2,3-trimethylcyclopentyl)hex-4-enal Chemical compound CC1CCC(C\C=C\CCC=O)C1(C)C DTHJNQYLRVNOCX-GQCTYLIASA-N 0.000 description 1
YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 description 1
NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 description 1
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AAPLYDDEQVREDC-UHFFFAOYSA-N 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal Chemical compound O=CC(C)=CCC1CC=C(C)C1(C)C AAPLYDDEQVREDC-UHFFFAOYSA-N 0.000 description 1
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
JFTSYAALCNQOKO-UHFFFAOYSA-N 3-(4-ethylphenyl)-2,2-dimethylpropanal Chemical compound CCC1=CC=C(CC(C)(C)C=O)C=C1 JFTSYAALCNQOKO-UHFFFAOYSA-N 0.000 description 1
ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 1
ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 description 1
ZOUVLXYJWNZBKG-UHFFFAOYSA-N 4-cyclopentylbutan-1-ol Chemical compound OCCCCC1CCCC1 ZOUVLXYJWNZBKG-UHFFFAOYSA-N 0.000 description 1
NRVFUNVHEXIEHU-UHFFFAOYSA-N 5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-3-en-2-one Chemical compound CC(=O)C=CCC1CC=C(C)C1(C)C NRVFUNVHEXIEHU-UHFFFAOYSA-N 0.000 description 1
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241000218645 Cedrus Species 0.000 description 1
JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 1
244000000626 Daucus carota Species 0.000 description 1
235000002767 Daucus carota Nutrition 0.000 description 1
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
239000005792 Geraniol Substances 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
241000234269 Liliales Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
244000272264 Saussurea lappa Species 0.000 description 1
235000006784 Saussurea lappa Nutrition 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
229940007550 benzyl acetate Drugs 0.000 description 1
JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
235000019506 cigar Nutrition 0.000 description 1
NPFVOOAXDOBMCE-PLNGDYQASA-N cis-3-Hexenyl acetate Natural products CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 1
RRGOKSYVAZDNKR-ARJAWSKDSA-M cis-3-hexenylacetate Chemical compound CC\C=C/CCCC([O-])=O RRGOKSYVAZDNKR-ARJAWSKDSA-M 0.000 description 1
235000000484 citronellol Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000834 fixative Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
229940113087 geraniol Drugs 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
VZLPDVOEBCMDIQ-UHFFFAOYSA-N hex-4-enenitrile Chemical compound CC=CCCC#N VZLPDVOEBCMDIQ-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
JPTOCTSNXXKSSN-UHFFFAOYSA-N methylheptenone Chemical compound CCCC=CC(=O)CC JPTOCTSNXXKSSN-UHFFFAOYSA-N 0.000 description 1
BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000008447 perception Effects 0.000 description 1
229940067107 phenylethyl alcohol Drugs 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/105—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
- C07C47/11—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings monocyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/105—Saturated compounds containing keto groups bound to acyclic carbon atoms containing rings
- C07C49/11—Saturated compounds containing keto groups bound to acyclic carbon atoms containing rings monocyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/21—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Nutrition Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Fats And Perfumes (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Cosmetics (AREA)
Seasonings (AREA)

ES07847910T 2006-12-08 2007-12-06 Uso de derivados canfolénicos como componentes de fragancia en perfumeria y aromatización. Active ES2373865T3 (es)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US87358606P	2006-12-08	2006-12-08
US873586P		2006-12-08
EP06291891A EP1930317A1 (de)	2006-12-08	2006-12-08	Verwendung von Campholenderivate als Duftstoff in Parfums und Aromastoffen
EP06291891		2006-12-08
PCT/EP2007/063435 WO2008068310A1 (en)	2006-12-08	2007-12-06	Use of campholenic derivatives as fragrant ingredients in perfumery and flavouring

Publications (1)

Publication Number	Publication Date
ES2373865T3 true ES2373865T3 (es)	2012-02-09

Family

ID=38066560

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES07847910T Active ES2373865T3 (es)	2006-12-08	2007-12-06	Uso de derivados canfolénicos como componentes de fragancia en perfumeria y aromatización.

Country Status (8)

Country	Link
EP (1)	EP1930317A1 (de)
CN (1)	CN101589021A (de)
AT (1)	ATE525347T1 (de)
BR (1)	BRPI0719945A2 (de)
DK (1)	DK2094650T3 (de)
ES (1)	ES2373865T3 (de)
PT (1)	PT2094650E (de)
RU (1)	RU2458048C2 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101723816B (zh) *	2009-11-26	2013-06-05	杭州友邦香料香精有限公司	一种2-亚龙脑烯基丁醛的制备方法
GB201115409D0 (en) *	2011-09-07	2011-10-19	Givaudan Sa	Organic compounds
FR2981070B1 (fr)	2011-10-11	2014-01-10	V Mane Fils	Nouveaux aldehydes cycloalcaniques, leur procede de preparation ainsi que leur utilisation en parfumerie
CN105517985B (zh) *	2013-09-06	2018-09-11	高砂香料工业株式会社	香料组合物
EP2962700A1 (de) *	2014-07-02	2016-01-06	Lucta S.A.	Kombination zur Geruchsbekämpfung
CN107735389A (zh) *	2015-05-29	2018-02-23	巴斯夫欧洲公司	具有1,2,2‑三甲基环戊烷‑1‑基结构部分的新型芳香化学品
CN114437021B (zh) *	2022-02-15	2023-05-09	东莞波顿香料有限公司	一种藿香香气化合物及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4052341A (en) *	1976-04-29	1977-10-04	Givaudan Corporation	3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol compound and perfume compositions
PL130019B2 (en) *	1981-07-15	1984-06-30		Process for manufacture of odorizing agent
US5288701A (en) *	1990-07-12	1994-02-22	Givaudan-Roure Corporation	Derivatives of dihydrocampholenic aldehyde
EP1067118B1 (de) *	1999-07-05	2004-03-31	Givaudan SA	Cyclopentylalkylnitrile und die Verwendung von Cyclopentylalkyl-Derivaten als Duftstoffe

2006
- 2006-12-08 EP EP06291891A patent/EP1930317A1/de not_active Withdrawn
2007
- 2007-12-06 RU RU2009126132/04A patent/RU2458048C2/ru not_active IP Right Cessation
- 2007-12-06 BR BRPI0719945-7A patent/BRPI0719945A2/pt not_active IP Right Cessation
- 2007-12-06 AT AT07847910T patent/ATE525347T1/de active
- 2007-12-06 PT PT07847910T patent/PT2094650E/pt unknown
- 2007-12-06 DK DK07847910.2T patent/DK2094650T3/da active
- 2007-12-06 CN CNA2007800454411A patent/CN101589021A/zh active Pending
- 2007-12-06 ES ES07847910T patent/ES2373865T3/es active Active

Also Published As

Publication number	Publication date
EP1930317A1 (de)	2008-06-11
RU2458048C2 (ru)	2012-08-10
PT2094650E (pt)	2012-01-05
BRPI0719945A2 (pt)	2014-04-22
ATE525347T1 (de)	2011-10-15
CN101589021A (zh)	2009-11-25
RU2009126132A (ru)	2011-01-20
DK2094650T3 (da)	2011-12-12

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ES2373865T3 (es)	2012-02-09	Uso de derivados canfolénicos como componentes de fragancia en perfumeria y aromatización.
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US20080138482A1 (en)	2008-06-12	Use of new campholenic derivatives as fragrant ingredients in perfumery and flavouring
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JP6016922B2 (ja)	2016-10-26	スミレ葉着香剤
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